


Criminal

by ChexLeMeneux



Series: My Dark Twisted Fantasy [1]
Category: Supernatural
Genre: 17-year-old Dean, Age Difference, Author Is A Total Pervert, Author Is Sleep Deprived, Babysitter Castiel, Babysitter cliche, Curious Castiel, Innocent Castiel, Inspired by My Fantasies, M/M, Picture Man of Steel Dylan Sprayberry as Castiel, Player Dean, Shy Castiel, Young Castiel
Language: English
Status: In-Progress
Published: 2016-09-20
Updated: 2016-10-12
Packaged: 2018-08-16 06:41:16
Rating: Not Rated
Warnings: Underage
Chapters: 3
Words: 2,882
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8091604
Author URL: https://archiveofourown.org/users/ChexLeMeneux/pseuds/ChexLeMeneux
Summary: Castiel decides to babysit Sam for extra cash, but the lingering eyes of one sly Dean Winchester catches him off guard.Castiel has a bit of a crush on Dean, while Dean himself prefers to onlyKeepItSimpleStupidAnd go for a nice lay, using every trick in the book to worm his way in between the tightly closed thighs of a curious young Castiel. He'll throw the book at him, the Ron Jeremy book, that is.





	1. Chapter 1

**Author's Note:**

> (Title inspired by Fiona Apple's "Criminal" which should give you a clue about my story.)  
> So, I'm in a jolly good sleep deprived mood, and I'm gonna write something erotic to take my mind off my other story.  
> I need something light, airy, and sexy--so I'll grab something from my 'Do Not Open' box and serve it up raw.

“Thanks, mister Winchester, I really need the extra money.” He says, smiling gratefully, shaking John’s hand excitedly.

“Dad, I don’t see why I need him to babysit me—I’m ten years old!” Sam protests, pouting.

“Sam, don’t be rude. He’s fourteen, you’re not. End of story. Now, Castiel, since I work from 9a to 7p, which means Sam would be home alone for four hours—and I don’t like that.” John explains.

“I understand; I’ll make sure to get him everything he needs during. Just curious, why can’t Dean do it again?” He asks, a bit confused.

“Well, Dean took up a second job—this one is 1p to 5p—which is still a lot of time alone,” John says, looking at Sam. The youngest Winchester folds his arms, huffing.

“Okay, got it. Well, once again, thank you. My other babysitting jobs are on hold since summer break is over,” he says, grateful.

“No problem, I trust you,” John says, patting Castiel on the and heading for the door. “Now, I’m a bit late—I’ll see you later boys!” He says, rushing out the front door.

“It’s not that I don’t like you Castiel, but I’d rather watch myself,” Sam says, walking away. Castiel watches Sam’s back as the kid stomps his way upstairs. Sighing deeply, he heads into the kitchen to prepare an afterschool snack.

.....

Pulling the Impala into the driveway, he shuts off the car—cutting off Metallica right as his favorite song starts. Yawning, he hops out of the car, heading for the house. The second he walks through the door; he’s greeted with fantastic smelling food.

“Whoa Sam, I’m surprised you didn’t burn down the house cooking!” He shouts, shrugging off his jacket and throwing it in the coat closet. When he gets no response, he heads for the kitchen—seeing no one. And suddenly, a young boy with the bluest eyes he’s ever seen pops up from the other side of the kitchen island—holding a pot-roast.

“Jesus!” He yells, startled by the boy. The kid doesn’t flinch, but he turns around, looking at the stove and then looking at Dean.

“You’re late,” he says, voice soft. The kid sits the roast on the island, pulling off his oven mitts. The food smells even better close up, the steam rising invitingly.

“Uh… who the hell are you?” He asks, and the boy gasps before looking greatly offended. The kid stalks off toward the living room—and Dean follows.

.....

As he’s heading into the living room, he’s still a bit awestruck by how… well, handsome Dean is. He hasn’t really seen him in a while, what with Dean ‘taking a break’ from school. Those green eyes… they are still very shocking but in a good way.

“Sam! I told you to text him, did you forget?” He asks with his hands on his hips. Sam doesn’t pull his eyes from the tv, still playing Left 4 Dead.

“Um, yeah, it slipped my mind,” Sam answers distractedly, quickly killing off a horde of zombies when the warning horn sounds off.

“Two things Sam, one, I said to text Dean so he wouldn’t be surprised and two, I told you to study before you play your games—now go!” He orders, putting power behind his voice, and Sam gets up at once—stomping off. He disappears into the kitchen, and then he returns quickly with his backpack, setting up his work in the living room.

“You handled that well, dude,” Dean says, chuckling. He smiles, glad to make Dean proud. “So, what’s your name?” He asks, and his jaw nearly drops to the floor. He’s heard many stories of the notorious Dean Winchester—not to mention they’ve been neighbors for like four years—and the guys doesn’t even know his name.

“C-Castiel, um, my name is Castiel. But my brother calls me Cassy,” he says, lowering his eyes.

“Wow, heh, that names a doozy and the nickname isn’t much better. I think I’ll call you… Cas,” Dean decides, nodding as he smirks.

“Uh, okay then… well, I have to go cook your dinner.” He says awkwardly, walking away quickly.

.....

This boy, he’s so strange yet so interesting. Plus, his eyes are to die for. And his body, that ass in those slacks—forget it! He quietly follows Castiel back into the kitchen, watching the boy from a distance. Leaning against the doorframe, he smiles, tumblers a-turnin’. Cas is young, which appeals to his better nature. The kid hums as he works his way around the kitchen, pulling muffins and cupcakes out of the oven and placing them on the countertop—oblivious. Those soft looking lips… and those shocking and jarring eyes… he decides then and there, he’s gonna do whatever he can to get that boy on his knees with his lips around his suddenly aching cock—looking up at him with those damn doe eyes. He chuckles, heading to his room upstairs.

.....

He doesn’t know why, but for some reason, he’s compelled to learn more about Dean. He’s watched him for years, said hi in passing, seen at grocery stores—all that jazz—but he’s never had the guts to say anything. He’s heard so much about Dean, about how he was a great student, sportsman, and-and even how he was great at… sex, but he never got the chance to find out if he was a nice guy, or what type of movies did he like, or what he did when he couldn’t sleep at night. And now, the opportunity has presented itself, and he’s gonna take full advantage. He finally gets to learn more, so that he doesn’t just have a crush on a handsome face and a nice body. Maybe, just maybe, he’ll be able to ask Dean if it’s alright to feel this way about other boys. He’s never had anyone to ask, knowing that Gabriel would tease him, but Dean might be nice about it—who knows, he could even like him back! Smiling, he sets out plates on the table.

“Dinners ready!” He calls, taking a seat.


	2. Chapter 2

**Notes for the Chapter:**

> Sorry it took so long to write this, haven't been exactly creative in the sex department lately. Enjoy, though.

It’s when they’re finished eating dinner that mister Winchester walks through the door, apologizing for being late and requesting a plate of Castiel’s wonderful smelling food. He served the older man, took his cash for the evening of service, and headed for the front door. But as he’s leaving, he feels a large hand wrap around his bicep. He turns around and is met with beautiful jade eyes and a handsome smirk.

“Dad said I should walk you home, it’s pretty late,” Dean says and he nods slowly, happily seizing the opportunity to spend alone time with him.

“Um, s-sure Dean, that sounds great.” He says, hopefully putting on a smooth smile instead of the dorky one he’s sure he’s sporting.

“Awesome, let’s go,” Dean says, taking him by the hand and leading him outside.

…..

As they walk a few blocks away, he gets curious. He saw the Impala in the parking lot—and the truck—so he’s curious as to why they’re walking.

“Um, so, do you drive?” He queries.

“Yep, too old to be depending on my old man for that,” Dean says, his hands in the pockets of his worn leather jacket.

“Wow, that’s awesome. I wish I could drive, the responsibility seems… stressful,” he says, smiling.

“Nah, it’s not too bad. You get to go wherever you want, whenever you want. Anyway, tell me about yourself, Cas.” Dean says, looking down at the younger boy with curious eyes.

“Um, well, there’s not much to know. I’ve lived in Kansas my whole life and I’ve always been a straight A student—oh! I recently started babysitting, too.” He says, rambling excitedly.

“Nice, you sound like a good kid. Me, not so much. D student in most classes, Sam is kinda the intelligent angel.” Dean says, chuckling deeply.

“You could be the same way, you know. All it takes is tenacity—”

“And this is fine-ass city, I know the spiel, Roger,” Dean says, laughing. And when Castiel makes a confused face, Dean just laughs more.

“Uh, whose Roger?” He asks with his blue eyes narrowed.

“The alien, dude, he’s hilarious. Anyway, what’re you doing Friday night?” He asks, smiling.

“Um, I don’t know, why?” He asks in return.

“I want to take you out, get to know you more. See if there’s anything beyond the blue eyes and nerddom,” Dean says, chuckling.

“Oh, sure—I’d love to. How’s 7 o’clock?” He asks, grinning hopefully. Dean shrugs, nodding.

“Sounds great, Cas,” he says and Castiel feels his cheeks heat—filled with excitement. “Maybe we can go roller skating—what do you say?” He asks and Castiel nods emphatically, smiling joyfully.

“I’d love to! I’ve never been roller skating before, I hope you’ll teach me,” he says, looking up at Dean through dark lashes.

“I’m kinda rusty, but I’ll show you what I know,” Dean says, flashing his signature grin.

…..

When they arrive at Castiel’s door, he’s not so sure he wants to say goodbye. It would be strange to ask if the boy will invite him in, but maybe it would be a good chance to—

“Thank you so much for walking me home, I appreciate it,” Castiel says, his pale face now filled with color.

“Anytime, I’ll be here on Friday. Wear something—”

“Who’s this, Cassy?” A boy asks, the front door of Castiel’s home being pulled open suddenly to reveal this sandy haired guy who looks like he’s nearly a midget.

“Um, this is Dean Winchester—he’s Sam’s older brother,” Castiel says. “This is my older brother, Gabriel.” He informs and Dean’s snaps into action, presenting his hand for Gabriel to shake—which the guy just stares at until Dean withdraws it.

“I’m gonna be taking Cas home every night, after he’s done babysitting my brother.” Dean says, slapping on a sly smile.

“We’ll see about that,” Gabriel mutters, rolling his eyes. “Thank you for bringing the baby home, much appreciated—see ya!” He shouts, pulling Castiel in the house swiftly.

“See you tomorrow, Dean!” Castiel says quickly, door slamming shut loudly.

“See ya, Cas,” he says, placing his hands in his pockets, smiling. “Tomorrow, lovely,” he says, chuckling.

…..

Once he’s in the house, he punches Gabriel in the shoulder like he was itching to do when Dean was here.

“Ow! What the hell,  _Cas_?” Gabriel asks, quirking an eyebrow. “Mad because I embarrassed you in front of your boyfriend?” He teases, folding his arms.

“He’s not my boyfriend! Just a crush,” he says, rubbing the back of his neck; uncomfortable. “He is a really cute and boyfriend material—but he’s too old!” He shouts, sighing as he plops down on their couch.

“Hey, it’s okay, you can totally woo him. You’ve got the eyes, little bro.” Gabriel encourages, taking a seat next to his little brother.

“I like him, not just for his looks, I’ve heard a lot about him. He’s nice, really Gabe.” He says, laying his head on his older brother’s shoulder.

“You can get him, bro, you just need the look. Dean Winchester is definitely a power-top, I can tell, so you really need to exploit this twink look you have.” Gabriel says and Castiel makes a confused face.

“What’s a-a twink?” He asks, cocking his head to the side.

“Well, a twink is a young gay boy. They usually have like zero body hair, kinda skinny—which is totally you, dude.” Gabriel explains and Castiel nods, understanding.

“But how do I exploit this look you’re talking about?” He asks, shaking his head confusedly. Gabriel gets this looks on his face… the one he gets before he’s about to get into mischief.

“It’s about time we get you a makeover, baby bro.” Gabriel says, chuckling to himself like a loon.

….

After two hours spent at the mall—hitting up H&M, Forever 21, Claire’s, Spencer’s—and buying $150 in clothes and-and makeup, they’re back home and he feels… really nice, actually. He doesn’t feel very good about the snakebite piercings in his lower lip, but Gabriel said he’d get used to it.

“Gabe, I-I think this might _actually_ work.” He says slowly, laughing lightly. Gabriel starts cackling, nearly dropping the several bags he’s holding.

“Okay Young Frankenstein, don’t get your hopes up.” Gabriel says, laughing a bit. “He’s gonna love this, I promise.” He says, smiling. Gabriel leaves him alone in his bedroom, to look at himself in his full length mirror. He’s in a clingy navy blue tank top, tight and ripped black skinny jeans, and the lip piercing…

“Oh, my god.” He whispers, touching his lip—flinching. “I hope you like the new and improved me,” he says, shaking his head.

**Notes for the Chapter:**

> Alright, I hope this was pleasing to those who like a slow build/burn. This was mostly establishing how he's changing himself to bend to what Dean might like, it gets worse folks. 
> 
> P.S. I hate, hate, HATE to ask for more views--but please take a look at The Witching Hour, thanks guys.


	3. Chapter 3

**Notes for the Chapter:**

> Sorry it took EIGHT FUCKING DAYS to crap out this chapter, but I haven't been in a very sexy mood. Too focused on my kids, but I'll do better. I promise :)

Beating his thumb against the steering wheel, he tries to think through his plans. He’s on his way home from work, Castiel will be in the house waiting, blue eyes practically twinkling—like they always do. He can tell the boy has a bit of a crush, so he’ll exploit that. Yeah, show the kid lots of attention, make him linger before sending him home—no, before taking him home. Smirking, he pulls into the driveway. He gets out quickly, walking up to the door and unlocking it; letting himself inside.

…..

“I’m home!” He yells, putting his leather jacket on the coatrack. “Where are you guys?” He inquires, walking through the house.

“We’re in the kitchen!” Sam yells, so he rushes over. He sees Sam cutting into some dough, shaping it into a ghost. Castiel is pulling a tray out of the oven, the smell of freshly baked cookies hitting him immediately but the only thing that makes his mouth water is the sight of Castiel. The boy is wearing small plaid boxers and a white t-shirt, smooth pale legs on display.

“Hello, Dean, we’re baking treat for Halloween.” Castiel says excitedly, placing the tray of assorted cookie shapes on the stovetop. He nods, walking over to the stove and reaching for what looks like a witch’s hat.

“Hey Cas, looks great. Mind if I—”

“No!” Castiel says sharply, slapping his hand. “They’re hot, you’ll burn yourself.” He says, not even acknowledging the assault. He grins, nodding once more.

“Alright, jeez, I’ll keep my hands to myself.” He says, raising his hands in surrender. Castiel smiles at him a little, and then he walks away to go back to his baking.

“What do you want to be for Halloween?” Sam asks him, taking him by surprise. He hadn’t really had any plans, but then an idea strikes him—a goal, really. By Halloween, he’s gonna fuck Castiel.

“Um, maybe I’ll go as Batman. What about you guys?” He asks and Sam’s eyes light up.

“I wanna be… Ant-Man! Ooh, or maybe I can be Spiderman, I don’t know just yet.” Sam says, stirring some cake mix happily.

“What about you Cas, what do you want to be?” He asks, leaning against the countertop. The boy shrugs, nonchalant.

“I’m not sure, Halloween isn’t really big at my house. Usually I just watch scary movies,” he says, using a rolling pin on more cookie dough.

“Well, maybe I can take you to a Halloween party. What you dress as if you could go?” Dean asks, wheels in his head turning quickly.

“If I could go, I’d want to be Robin. With the mini-shorts and everything,” he says, smiling shyly to himself. Picturing Castiel in those tiny green shorts… his cock is hard almost instantly, damn near painfully.

“That’s-that’s really cool Cas, um, I’m gonna head upstairs.” He says abruptly, but the boys take it in stride.

“I think that costume is a bit lame, dude.” Sam says and the boys both start laughing, him quickly dashing out of the kitchen.

…..

Upstairs, he rips of his jeans immediately, pulling out his smartphone and heading straight to pornhub. Typing ‘Batman and Robin’ in the search, he finds several pornos with small, twinkish guys. He smiles, lying down in his bed. In the video, there are some horribly delivered lines, worse than the ones from the 60s. But suddenly, Batman is rubbing Robin’s thigh, touching him intimately. They start to kiss, Batman pulling off Robin’s short-shorts slowly. Wrapping a hand around his cock, he starts stroking his cock, biting his lip to keep in the moans.

“Fuck,” he hisses out, increasing the pace when Batman starts fingering Robin’s tight, hairless hole.

“Golly gee willikers, Batman.” Robin moans, throwing his head back in the seat of the Bat-Mobile. He pumps his hand faster, seeing that they’ve cut to Batman slowly rubbing the head of his big cock against Robin’s pink pucker. He comes immediately, thinking of Castiel’s blue eyes wide with panic and pleasure.

…..

Panting, he comes down from his euphoric high, still seeing those blue eyes in his mind. Going to his bathroom, he washes his spunk off his hands. He sees himself in the mirror, pupils blown wide, lips red from he bitten.

“Fuck, what kind of hold do you have on me?” He whispers to himself, shaking his head as he goes back to his room. Plopping down on his bed, he pulls out his phone again. Typing into the Google search ‘Robin outfits’, aiming to find something… skimpy.

**Notes for the Chapter:**

> Hope you liked it, if you didn't, I totally understand. I plan on balancing watching my kids, studying for the GED, and sleeping. I swear, scouts honor.

**Author's Note:**

> I hope you guys liked this considering it's been a while since I wrote something remotely sexual--well, that's not entirely true.  
> Any hoosa poosa, I'm gonna write a new series of pervy things. Seriously, picture young Superman from Man of Steel--that Dylan Sprayberry guy is seriously who I think of when I imagine a young Castiel.  
> He's got the eyes!  
> If you want this to go in a certain direction, hit me up. If you think I should continue, hit me up. If you want to kiss my ass early, shoot me some kudos. Peace. Out!!


End file.
